Bitchy MILF and the Delivery Boy

This story is a work of fiction. It is only my imagination. There is no underage sexual activity in this story.

My name is Jimmy, and I just had the wildest time of my life. I found out something about myself that will shape my sex for the rest of my days.

I started working in the local grocery store when I was 18 years old. My job was to bag groceries at the checkout lines. I liked it because I got to see every female that came through the store as they waited in line for me to finish bagging their items.

I wanted to start saving money so I could go to college and do something with myself. I didn't plan on keeping this job for long. I worked as many hours as I could get. I still lived with my parents so I was saving money there as well.

I had a couple of buddies I hung out with now and then, but never had a "best friend." When I was in high school, most of the kids thought I was a geek, or a freak. I was tall, 5'11", and skinny and lanky. I had brown hair and green eyes. I wasn't the best looking guy around, but I wasn't ugly either.

The one thing I did have going for me was my cock. I was blessed with an unusually large one. It was 7 inches when soft, and almost as big around as that cardboard roll on the inside of the toilet paper. I know because I stuck it in there one day, and it was a very snug fit.

Anyway, when it got hard it grew to 11 inches, and would not fit in that toilet paper roll any more. I have since seen porno films of John Holmes, and I could relate to that guy for sure.

No matter what I wore, it looked like I had a pair of socks stuffed down my pants. For a time I took to wearing long baggy shirts to hide it so I wouldn't have to put up with people staring at it all the time. It was pretty embarrassing when I would catch people looking at it. I was shy and would look away, or just pretend I didn't see them looking.

However, once I started watching porn movies and realized it could be an asset, I said fuck it and wore what I wanted." Let them look" I thought. I could care less one way or the other from now on.

I started wearing sunglasses when I was out so I could watch them without them knowing. When the women didn't think I could see them, it got very interesting. I started wearing clothes that made my bulge very noticeable, and I was having fun now.

I started to like the looks. Girls my age would check it out, and most would giggle and whisper to each other. I got used to that. If they were alone, some almost looked scared, or horrified, and would turn away.

The older women were another story. I especially liked the looks from them. When they checked me out it really turned me on. I started to try harder to let any older women get a good look at my bulge.

Just about every one of them would look at it, do a double take, glance up to my face, and always glance back down to my crotch again before looking away. Some couldn't help licking their lips. And the look in their eyes when they did that said it all. They knew what was there and they knew what to do with it.

When they did that I would think of them sucking it, or fucking them with it. I knew I had to have one of them one day, just to let them see it and show me what a real woman would do with it.

A month after I started working, an older woman moved to our town. She didn't wear a wedding ring, and there was no sign of a man living with her. She would come in a couple of times a month for her supplies.

I figured she had to be 50 if she was a day, but she had a really nice body. Her hair was dirty blonde, shoulder length, with blue eyes and nice full lips that were always covered in bright red lipstick. Her tits had to be 44 DDD or something. They were huge. She had a bit of a belly but a small waist, and legs that went all the way up to her nice plump ass.

For an older woman, I thought she was hot! I wanted to fuck her from the minute I laid eyes on her. Every time I saw her I thought of sucking those big tits, and fucking her with my big hard cock.

She didn't dress to show off, but she couldn't help looking hot no matter what she wore. It didn't matter if she wore jeans and a sweater, or a skirt and blouse. She would look sexy in a burlap sack, and I would watch her walk by as she went up and down the aisles, and wait for her to get in line for check out.

Her only fault was she was a bitch! Actually, she was an asshole to be more precise. From the first time I bagged her groceries, she complained about everything. She had more rules about bagging than my boss did.

"Don't put those cans with that box," She would say.

"Yes Mam" I would reply.

"Put that in a bag by itself young man," she would bark.

I would grab a new bag and say "yes Mam, sorry about that."

On and on she would go. "That's too much in that bag." "Put more in that bag."

As much as I loved to look at her body, I hated it when she came to my line. I would get really pissed off but didn't dare say anything to her. I wanted my job so I bit my tongue and did what she told me to do.

It's a good thing she only came in a couple of times a month. Every time she came to my line I would listen to her complain, and fantasize about stuffing her mouth with my cock so I wouldn't have to hear her bitch at me. She always had a sour puss on her face and an attitude no matter what.

All the employees would complain about her. I would hear things like "she needs a man" or "if she got laid once in a while she might lose that attitude." They all felt sorry for me because she treated me the worst of all the workers in the store.

I didn't think she was interested in men. The one time she looked at my crotch, she just stared at it for about 5 seconds. No double take from her. When she looked up to see me looking at her, she did a little roll of the eyes and had a frown on her face like I just farted and she knew it was me.

I quickly looked away and felt embarrassed for the first time in a long time. I figured she must hate men and cocks and that's why she was such a bitch. I tried to avoid her as much as possible after that and prayed she would go to another line when she came in the store.

About a year after working there, my boss decided to try phone orders with local delivery inside a 10 mile radius. We lived in a pretty small town so that included most of the people in town. I knew where Mrs. Jones lived, and I was positive it was more than 10 miles from the store, so I knew she would still be coming in and harassing me.

Then my boss called me in his office. He said "Jimmy, since you own a car, how would you like to try delivering the groceries when we get a phone order. I'll pay you for gas and you won't have to bag any more. You can switch to stocking shelves until we get a phone order. When someone calls in an order, you fill it and deliver it. What do you say?"

I was thrilled and told him so. "Absolutely Boss" I said. "I would love to do that instead of bagging." Best of all, I knew Mrs. Jones lived more than 10 miles from the store. I wouldn't have to deliver to her OR bag her groceries any more. Not having to deal with her was the best perk of the job now, and I was a happy kid.

From then on I would I just watch her shop when she came in, and think about fucking the shit out of her to teach her a lesson. I wanted to stuff her mouth with my cock so she couldn't talk any more. That was my new fantasy and I had it every time she came in to do her shopping.

Everything went great for a couple of months. I loved my new job. I would watch Mrs. Jones walk around the store if I was there when she came in, and imagine all kinds of nasty things to do to her. She would bitch at everyone else but me, and I loved it.

Then one day I saw Mrs. Jones in the office with the manager. I couldn't hear what was being said, but I could tell she was mad as hell. Her arms were waiving all over the place and she was pointing her finger at him. Her mouth was going a mile a minute the whole time.

Every time he tried to say something she cut him off. He just sat there and let her bitch. Then he said something to her, and she turned and stormed out of his office. She kept right on walking and left the store.

When I heard my name over the P/A system to report to the manager's office, I knew it wasn't going to be good. I dropped what I was doing and headed back to his office to see what was going on.

He was seated at his desk looking like his dog got run over by a car or something, and told me to have a seat. "I'm sorry Jimmy" he said, "but you're going to have to make deliveries to Mrs. Jones' house from now on."

I couldn't believe he just said that! "But she lives about 15 miles from the store" I said, "and the policy is 10."

"Well, it's actually 12 miles" he informed me, "and she threatened to sue me if I don't make an exception, and I don't need the hassle or the expense to try to fight her about it."

I just sat there staring at him, thinking about telling him I wasn't going to do it. I wondered if I would get fired if I did. I thought about it for a minute, and said "do I have to if I want to keep my job?"

He sighed and said "you're a good kid Jimmy, and I won't fire you, but I'm asking you to do it for me so I can avoid any problems."

He had been very good to me since I started working there, so I said what the heck and agreed to do it. He thanked me, shook his head, and said "good luck with that one, she's a beauty."

Of course she called in an order the very next day. I was a nervous wreck as I filled it. I dreaded going to her house and just knew it was going to be hell. I didn't want to lose my job, but then again, I didn't want to take any more shit from this bitch either. I don't care how good she looks.

On the drive over I tried to think of a way to handle her if she got shitty with me. She was an asshole and someone needed to put her in her place one of these days. I realized I wasn't going to be the one to handle that job right now, and resigned myself to delivering the groceries and getting out of there as quickly as I could.

I pulled up to her house, and there she was, standing in the door, waiting. "Great" I muttered to myself, "just keep your cool and get in and out of there Jimmy, you can do it." I watched her standing there for a minute, then took a deep breath and got out of the car. I grabbed all 4 bags and turned to go in the house.

She opened the door and yelled "don't carry all of them at once, you'll drop something."

I said "it's ok Mrs. Jones, I have it under control."

She stepped out on the landing and raised her voice higher; "young man, I said DO NOT carry them all at once, now put two of them down and make two trips!"

I turned around and set 2 of them on the hood of the car, and carried the other two across the lawn and up the steps to her door. She just stood there glaring at me, and I had to wait a few beats for her to get out of my way so I could bring them in the house.

She stepped inside the door and pointed to the kitchen table. "Set them on the table and go get the other two" she said with an edge.

I set them on the table, apparently a little too hard for her, and she yelled "don't you slam those bags young man, if you break something you will pay for it."

"Yeah yeah" I mumbled under my breath as I stepped by her and went out the door to get the other two bags.

I still heard her as I was crossing the yard to my car; "I heard you young man, don't you dare be insolent with me." I didn't hear the rest of it and didn't care what she said. I grabbed the other two bags and went back in.

As she stood there glaring at me, I brought the other two bags in and smiled at her as I gently set them on the table

As politely as I could, I said "that will be $37.00 Mrs. Jones."

Typical bitch that she was, she replied "I know how much it is young man," as she picked up a check off the counter and handed it to me.

I said thank you and turned to leave. As I was walking out she said "I will speak to your boss about this, and I better not have to deal with your insolence again."

I turned to say something, but just stood there looking at her. As I checked out her big tits and that red lipstick, all I could think of was my cock stuffed in her mouth, and the only noise coming from her would be her gagging on it. That image made me smile again, and I kept my mouth shut and walked out of her house.

I had to explain the situation to my boss when I got back. He told me his ear was still burning from her phone call. He said he believed my version of how it went, and told me to handle it as best I can. He reminded me to be respectful and polite at all times.

I told him I would do my best because I didn't want to lose my job. I knew it wasn't going to be easy, but I vowed to ignore her and be as polite and respectful as I could no matter what she said to me.

That is, until I found a better job. I was looking very hard and putting in applications all over and hoping for the best. As soon as I found one Mrs. Jones was going to hear it from me. I didn't care how hot she looked. I couldn't wait for that last delivery.

And that's how it went for the next three months. Every delivery was a nightmare from the minute I pulled in the driveway until I got back in the car to get out of there as fast as I could.

She bitched about everything. "You're late." "This bag is too full." "Don't put it there, put it over here."

I would ignore her and do what she said. That pissed her off even more. She would start yelling "I'm talking to you young man, do you hear me?"

I would just say "yes mam," and "no mam," and do whatever it took to get it done and get out of there. I knew that every delivery brought me closer to the day I would let this bitch have it.

The only difference now being, I was no longer thinking of telling her off. I wanted to stuff her mouth with my cock like I had been fantasizing for over a year now. I even thought about fucking her in the ass now. That would teach her a lesson. I just wanted to shut her up, and it's all I thought about every time I had to put up with her abuse.

After those few months of her abuse, I found another job. I gave my boss his two week notice, then waited for that delivery to Mrs. Jones. I didn't have to wait long. She called in her order the next day.

On that day, I got her order filled and headed on over to her house. I told myself this is the day I set this bitch straight. I knew I would only end up telling her off. As much as I wanted to stuff her mouth with my cock to shut her up, I wasn't going to rape her to do it. It was just fantasy and I would settle for telling her off but good. It made me feel better and I knew I was going to enjoy this visit, I just didn't realize how much.

I arrived with her usual 4 bags, and grabbed all of them and headed in to the house. She was standing in the door as usual, and she opened it up right away and said "I've told you before, only TWO at a time, now put those other bags down and make two trips."

I ignored her and with a big smile just walked across her yard and in to the house. The whole time she was going on and on about it. "Did you hear me young man, I said to carry two at a time and make two trips."

I just smiled and walked past her in to the kitchen and dropped them on the table. She was still bitching at me when I turned around, looked her dead in the eyes, and said "shut the fuck up bitch!"

I have to say, that was the funniest expression I have ever seen on anyone's face in my whole life. Her mouth was wide open, her eyes were round as saucers, and she had the most dumbstruck look on her face I've ever seen, before or since.

She then stammered "wha-wha-what did you just say to me?"

I took a step closer and said "you fucking heard me; I said shut the fuck up bitch, before I shove my cock in your mouth and shut you up myself!"

She took in a sharp breath, then put her hands on her hips and glared at me. She then let her eyes travel down to my crotch, stared at it for a full ten seconds, then looked back up at me and said "you wouldn't dare."

I reached for my zipper, and as I started to lower it I said "oh no? You don't think so bitch? You don't think I'll stuff your fucking mouth full of cock?"

Then she did it and I knew I had her. She licked her lips. Her eyes were glued to my hands as I unzipped my fly all the way and slowly reached in my pants. With her eyes watching every move, I pulled my cock out of my pants and let it hang there. Her eyes widened at the size of it, and it wasn't even hard yet.

I put my hands on my hips and stood there watching her. I figured it's all or nothing now, so I went for it. "You like that big cock don't you?" I said as I grabbed it and stroked it nice and slow.

She stood there, transfixed, unable to take her eyes off my cock. There was a hunger in her eyes that I had never seen on any woman who checked me out. Maybe that's because none of them had seen my cock in the flesh, only the bulge in my pants. Whatever it was, this lady wanted my cock and now I knew it.

"Yeah, I like you a lot more this way, with your big mouth shut" I said as she continued to stare at my hand going back and forth on it, "now get over here and get on your knees so I can give you something to do with that mouth besides bitch."

She took two steps and fell to her knees, her eyes never leaving my hand as it stroked my cock to an erection. She started to pant heavily and her hands grabbed those huge tits and squeezed and massaged them, making her moan as she stared in awe at the size of my cock, which was starting to get hard and had grown a couple of inches as she watched.

It was now at full erection, and I held it at the base so the full length was sticking straight out in her face. I shook it at her like a stick, and stepped right up to her to rub it on her lips.

"What the fuck are you waiting for" I growled at her, "suck it bitch!"

She grabbed my cock with both hands and took the head in her mouth. She sucked on it hungrily, stopping to kiss the head then suck it back in her mouth. Her left hand was holding it near the base while her right hand stroked it back and forth. She spit on it and jerked it faster. Then she moaned and rubbed the head all around her face, over her lips, then licked the shaft up and down the sides. The entire time she was whimpering like the bitch in heat that she was.

I loved it. I was going to get my revenge for almost 2 years of her bullshit. The more I thought of it the angrier I got, so I grabbed her by the hair and forced my cock in her mouth, trying to push it down her throat. She gagged but didn't stop at all. To my surprise, she moaned louder and seemed to like it even more.

I started talking nasty to her then. "You like that bitch?" "You like your mouth full of hard cock?" I taunted.

The more she moaned the more I talked. "You like when I fuck your mouth don't you?" "You want me to treat you like a fucking whore don't you?"

As soon as she heard "whore" she went wild, slipping my cock out of her mouth and saying "yes, I'm a whore, I'm a dirty fucking whore that wants your big fat cock."

Now it was my turn to moan. I was shocked and thrilled at how this was going, and I wanted more. "Suck it then, suck my fucking cock you whore" I yelled at her.

As she sucked me like a wanton whore, I reached down and ripped her shirt open, then pulled her bra up over her tits. She let my cock slip out of her mouth and let go of it so I could slip her bra up over her head. I grabbed her big tits and squeezed them hard, pinching her eraser size nipples as she moaned with pleasure.

She grabbed for my cock, spit on it again, gave it a couple of strokes, then stuffed it back in her mouth, sucking it and slobbering all over it. She was acting so nasty and I was getting off on it big time.